Deer Santa Festival

Picture Pittsfield is announcing a date change of the Annual Deer Santa Festival. The fourth annual Deer Santa Festival will now be on Sunday, Dec 4, 2022. WE ARE ONLY IN THE PRELIMINARY PLANNING STAGES. WHAT FOLLOWS IS WHAT TOOK PLACE IN 2O21. CHECK BACK IN APRIL FOR DETAILS OF OUR 2022 FESTIVAL.

Photos with Santa

Time and Location TBD

Dance Performance

We will have a special performance from S&S School of Dance

Help Decorate the Community Christmas Tree

The Pike County Art Guild will be hosting an Ornament & Mug Decorating from 2:30-4:30 p.m. on Sunday November 28, 2021. Decorated ornaments can be placed on the Christmas Tree afterwards.

Story Book Stroll

The library is hosting a story book stroll sponsored by DOT foods on the west side of the square!


We invite any groups or churches who would like to sing carols on the courthouse steps between 3:30 and 5:00 p.m. Send an email to to be on our list, please also include your song choices so we can avoid duplicates!

Live Reindeer

We are currently working on getting a live reindeer from 3-5 p.m. Will announce once confirmed.

Lighted Parade

Picture Pittsfield will host the second Deer Santa Festival Parade on Sunday, November 28, 2021 at 5:15 PM.
Line- up will begin at 4:30 PM at NAPA Auto Parts at 113 E. Jefferson St. (corner of Jefferson and Madison) in Pittsfield.

Because this is our first lighted parade and held in late afternoon, we are keeping it short and sweet. The parade will go from NAPA south on Madison, left on Washington) and around the Square turning north on Monroe, then back to NAPA where it will disperse.

This year’s parade theme will be “A Picture Perfect Christmas”. Entries can depict Christmas celebrations from the past, current times, or even the future. Or any idea you come up with. Use your imagination and have fun! Entries will compete in three categories: Families, Businesses, and Organizations/Schools. Awards will be given. Parade entries should have a sign identifying the group for the judging.

Again, this is a LIGHTED parade and will be judged for lighting, but all entries are welcome. Awards will be given out for first and second place winners. All entries should be submitted no later than Wednesday, November 24, 2021. You must submit a separate form for each entry, (float, marching, walking, golf cart, dance, etc.)

Email completed entry forms to: If you need to submit your entry by hard copy,
please call or text Kaye Iftner at 201-314-3624 for pickup, or drop them off at Pikeland Motors before Thursday, November 25. Please direct all questions to Kaye Iftner, parade chair at 201-314-3624 or by email at:

Christmas Tree Lighting Ceremony

Help us kick off the holiday season by lighting the Christmas Tree at 5:30 p.m.

Holiday Market

We invite any vendors to set up on the square. There will be no charge, but you must have insurance. E-mail questions to Forms can be found below. Again, there will be no charge to set up, but we do need you to fill out the forms.

Deer Santa Yard Deer Display Challenge – Deer will be on display during the festival. We had 47 deer on display in 2019… we’re hoping to grow the herd even bigger! You can purchase a blank wooden yard deer through Picture Pittsfield for $40 ($30 cost, $5 donation to the Pittsfield High School wood shop for cutting out the deer for us and $5 donation towards the Deer Santa Festival expenses). Pickup from Pikeland Motors. 118 N. Monroe St., Monday through Friday, 9 a.m.-5 p.m. Deer will be sold on a first-come, first served basis, no holds or pre-orders. When you pick up your blank deer, please pay the $40 cost by cash or check made out to Picture Pittsfield only – no credit or debit cards.

If you have a deer from previous years, you can enter it as is, or redecorate it. To enter your previous year’s deer in the display, it will be a $10 donation, cash or check made out to Picture Pittsfield. These donations will go toward Deer Santa Festival expenses and materials. The $10 is payable at deer display drop off on Nov. 28.

Decorate your deer any way you like (family friendly, please!), give it a name, and then deliver it back to the Pittsfield courthouse square between 11 a.m. and 2 p.m. Nov. 28 so that Picture Pittsfield volunteers can add it to the display.  Be sure to give it to a Picture Pittsfield volunteer so the proper info can be recorded for your entry in to the contest. Top deer will win fun prizes! Deer need to be removed from the courthouse lawn by their owners between Sunday, Jan. 2 and Wednesday, Jan. 5, 2022.

Some of the 2019 Deer Santa Display entries.

Christmas Wreath Auction at the old Red Dome Lobby

Businesses and individuals are invited to “adopt” an undecorated wreath from Pikeland Motors for $10, decorate it, and then return it for display. Wreaths will be displayed in the old Red Dome Lobby area, (the lobby for Brewed, Reap & Sow, and Pike County Mercantile). Wreaths will be sold on a first-come, first served basis. This year a virtual silent auction will take place via a Facebook event. A silent auction for each wreath will begin Nov. 28 and continue through 5 p.m. Thursday, Dec. 9. At that time, the silent auction will close and wreath winners notified. Proceeds benefit Picture Pittsfield’s 2022 local community projects. Details on the virtual silent auction can be found here.

Letters to Santa

Between Sunday Nov. 28-Friday, Dec. 17, children can “mail” their letters to Santa by dropping them off at Santa’s House on the Courthouse Lawn. Any letter with a mailing address will be answered! A big thank you to the city’s front office staff for making this possible!

Letters to Santa can be “mailed” at Santa’s House on the Pike County Courthouse Lawn.

“Light It Up Pittsfield” Holiday Decoration Contest – Dec. 17, 2021, 5:30-8:30 p.m.

Here’s your chance to officially become the Clark Griswold of Pittsfield! Picture Pittsfield volunteers will be touring the city between 5:30-8:30 pm Friday, Dec. 17 and selecting two outdoor holiday decor winners: Business and Residential. Business are office buildings, shops and restaurants. And residential entries are decorated homes, any size and shape. Residences and businesses must be within the Pittsfield city limits. A winner and runner up will be selected in each category for a total of four winners. Entries will be judged on creativity and overall attractiveness.

Categories:  Residential (houses, duplexes, apartments) and Business (window or store front /locally and commercially owned).   Each category can win 1st Place and Runner Up.

The things judges will be looking for:

Lights – We are looking for brightness, colors, organization and movement.

Theme – We will be looking for Christmas themes. Think movies, songs, stories,  etc. 

Spirit – We are looking for the house or business that encompasses what Christmas is all about.  

Residential and businesses will be judged on a scale of 1-5 

5.  Beyond Exceptional

4.  Exceptional

3.  Middle of the Road

2.  Best Attempt

1.  Minimalist

Be sure to have all lights and animation on between the hours of 5:30-8:30 pm Friday, Dec. 17. If you would like your business or residence to be judged then please fill out this form by Sunday, Dec. 12, 2021. If you questions, you can email them to

The Deer Santa Festival was launched in 2019 as a project of the community organization, Picture Pittsfield. Area businesses and organizations host holiday activities around the community and are listed on one community calendar. The festival kicks off with a Santa Parade and Christmas Tree Lighting event the Sunday after Thanksgiving and activities continue through December.